Cortona to San Gimignano and Montepulciano: Private day trip

With strict restoration rules, San Gimignano has maintained its authenticity and history to this day. Considered a gem in the Tuscan region and just a stone’s throw from Florence, this town has always had a favorable location. Its beautiful surroundings and elevated position made it the perfect relay point for those on pilgrimage to Rome. A special must-see in San Gimignano are its 14 towers - the survivors of an original 72. Admire the Romanesque and Gothic architecture while discovering one of the many museums holding some of the most coveted Italian artworks of the 14th and 15 centuries. Afterwards, take a walking tour of the inner-city walls. Yes, they are two! San Gimignano is protected by a set of two walls, which are accessible by various entries both from the inside and outside of town.

Montepulciano is renowned for its pork, cheese, "pici" pasta, lentils, and honey, but it's known worldwide for its wine. Connoisseurs consider its Vino Nobile among Italy's best. The city, full of elegant Renaissance palaces, ancient churches and hidden corners, boasts vast panoramas all over the wonderful Val d'Orcia and Val di Chiana valleys that surround it. It has one of the most intact and architecturally unified historic centres of any Italian town: within its walls, no major building work has taken place since 1580. Piazza Grande is the heart of Montepulciano and the setting for its main events, including the Bravio delle Botti barrel racing contest held in August every year and much more. Just be prepared to share the town: Montepulciano has received great attention following the filming of the vampire saga Twilight sequel New Moon here and has seen a notable increase in visitors.